Sequential Heck–Heck reactions for the dibenz[a,f]indolizine skeleton: synthetic application to decumbenine B

Lee, Bok-Jin; Hong, Gil-Pyo; Kim, Guncheol

doi:10.1016/j.tetlet.2016.10.064

Cited by 9 publications

(5 citation statements)

References 27 publications

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“…Oney ear later,K im reported as equential Heck reaction of benzamidoacrylatesw ith Pd(OAc) 2 and NaHCO 3 to render an indolizine-fused isoindolinone ring as part of the strategyf or the total synthesis of decumbenine B (Scheme 45 B). [100] Polycyclic isoindolinones can be efficientlys ynthesized by palladium catalyzed dearomativet ransformations. Dearomative Heck reactions of indoles have been reporteda sa ne fficient methodf or the construction of indoline-fused isoindolinone skeleton containing quaternary stereocenters.…”

Section: Pd-catalyzed Cyclization Via Dearomatization/heck Reactionmentioning

confidence: 99%

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Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Savela

Méndez-Gálvez

2021

Chemistry A European J

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Isoindolinone structure is an important privileged scaffold found in al argev ariety of naturallyo ccurring as well as synthetic, biologically and pharmaceutically active compounds. Owing to its crucial role in anumber of applications, the synthetic methodologies for accessingt his heterocyclic skeleton have received significant attentiond uring the past decade. In general, the synthetic strategies can be divided into two categories:F irst, direct utilization of phthalimides or phthalimidines as startingm aterials for the synthesis of isoindolinones;a nd second, construction of the lactam and/or aromatic rings by different catalytic methods, including CÀHa ctivation, cross-coupling,c arbonylation, condensation, addition and formal cycloaddition reactions. Especially in the last mentioned, utilization of transition metal catalysts provides access to ab road range of substituted isoindolinones.H erein, the recent advances (2010-2020) in transition metal catalyzed synthetic methodologies via formation of new CÀCbonds for isoindolinones are reviewed.

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Section: Pd-catalyzed Cyclization Via Dearomatization/heck Reactionmentioning

confidence: 99%

“…One year later, Kim reported a sequential Heck reaction of benzamidoacrylates with Pd(OAc) 2 and NaHCO 3 to render an indolizine‐fused isoindolinone ring as part of the strategy for the total synthesis of decumbenine B (Scheme 45 B). [100] …”

Section: Cross‐coupling: Annulation/cyclizationmentioning

confidence: 99%

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Savela

Méndez-Gálvez

2021

Chemistry A European J

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“…6 In 2016, Kim reported a domino catalysis using palladium-catalyzed intramolecular double Heck reactions to construct the 5-membered ring and 6-membered ring sequentially (Scheme 1b). 7 In 2019, Kumar described a relay catalysis in which enamides were formed through copper-catalyzed Sonogashira coupling followed by intramolecular cyclization, and then obtained isoindolo[2,1- b ]isoquinolin-7(5 H )-one derivatives via a subsequent intramolecular Heck reaction (Scheme 1c). 8 In 2018, Reddy reported a Rh( iii )-catalyzed cascade annulation involving the combination of a [Cp*RhCl 2 ] 2 -catalyzed domino catalysis and a base-mediated intramolecular addition of amide nitrogen to aldehyde (Scheme 1d).…”

Section: Introductionmentioning

confidence: 99%

Construction of indolizine scaffolds from α,ω-alkynoic acids and α,ω-vinylamines via sequential-relay catalysis in “one pot”

Liu,

Lu,

Zhu

et al. 2024

Org. Biomol. Chem.

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“…In 2016, the Kim research team completed the formal synthesis of decumbenine ( 66 ) via double Heck reactions (Scheme 4d). 20 When diiodide 63 was allowed to react with Pd(OAc) 2 and sodium bicarbonate, hexacycle 64 was obtained in 40% yield via tandem Heck reactions. Decarboxylation of 64 was achieved under basic hydrolytic conditions to give 65 in 40% yield.…”

Section: Introductionmentioning

confidence: 99%

“K‐synthesis”: Recent advancements in natural product synthesis enabled by unique methods and strategies development in Korea

Han

2022

Bulletin Korean Chem Soc

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Natural product synthesis has lain at the heart of organic chemistry. Complex structures of natural products have inspired chemists to develop new methods and strategies. The utility and robustness of newly developed methodologies have been tested by their application into total synthesis. With the necessity to establish a solid health-related and biomedical Korean industrial ecosystem, a historically belittled sector when compared to well-invested manufacturing and electronics industries in Korea, there has been enormous recent progress in the Korean organic chemical research. Accordingly, impressive syntheses of complex secondary metabolites that feature unique tactics and ingenious strategies have been reported by synthetic organic chemists in Korea. Herein, recent advancements (mostly after 2010) in natural product synthesis from Korea are depicted. Representative accomplishments from researchers in Korea are presented with an emphasis on unique methods and strategies that are utilized into their synthetic approaches.

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Sequential Heck–Heck reactions for the dibenz[a,f]indolizine skeleton: synthetic application to decumbenine B

Cited by 9 publications

References 27 publications

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Construction of indolizine scaffolds from α,ω-alkynoic acids and α,ω-vinylamines via sequential-relay catalysis in “one pot”

“K‐synthesis”: Recent advancements in natural product synthesis enabled by unique methods and strategies development in Korea

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